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303585

Sigma-Aldrich

2-Amino-5-nitrophenol

Synonym(s):

2-Hydroxy-4-nitroaniline, 3-Hydroxy-4-aminonitrobenzene, 3-Nitro-6-aminophenol, 5-Nitro-2-amino-1-hydroxybenzene, 5-Nitro-2-aminophenol, NSC 7087

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About This Item

Linear Formula:
H2NC6H3(NO2)OH
CAS Number:
121-88-0
Molecular Weight:
154.12
Beilstein:
972974
EC Number:
204-503-8
MDL number:
MFCD00007692
UNSPSC Code:
12352100
PubChem Substance ID:
24858130
NACRES:
NA.22

form

solid

mp

198-202 °C (dec.) (lit.)

SMILES string

Nc1ccc(cc1O)[N+]([O-])=O

InChI

1S/C6H6N2O3/c7-5-2-1-4(8(10)11)3-6(5)9/h1-3,9H,7H2

InChI key

DOPJTDJKZNWLRB-UHFFFAOYSA-N

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Application

2-Amino-5-nitrophenol was used:
  • as starting material in the synthesis of series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl) hydrazine carboxamides
  • as semipermanent (nonoxidative) hair colorant and as toner in permanent (oxidative) hair dye products
  • in synthesis of series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones, anticonvulsant agents
Reactant for:
  • Diazotation and coupling reactions
  • Preparation of biologically and pharmacologically active molecules

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nadeem Siddiqui et al.
Archiv der Pharmazie, 343(11-12), 657-663 (2010-11-27)
A series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl) hydrazine carboxamides (6a-r) was synthesized using 2-amino-5-nitrophenol as a starting material. All the synthesized compounds possessed two hydrogen-bonding domains and their effect on the activity was studied thereof. The anticonvulsant activity was assessed by
Christina L Burnett et al.
International journal of toxicology, 28(6 Suppl 2), 217S-251S (2010-01-30)
2-Amino-3-nitrophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 4-amino-3-nitrophenol, 4-amino-2-nitrophenol, 2-amino-4-nitrophenol sulfate, 3-nitro-p-hydroxyethylaminophenol, and 4-hydroxypropylamino-3-nitrophenol are substituted aromatic compounds used as semipermanent (nonoxidative) hair colorants and as toners in permanent (oxidative) hair dye products. All ingredients in this group except 2-amino-4-nitrophenol sulfate, 2-amino-5-nitrophenol, and 4-amino-2-nitrophenol
F Chen et al.
Cancer letters, 126(1), 67-74 (1998-05-01)
Two hair dye components, carcinogenic 4-nitro-2-aminophenol and 5-nitro-2-aminophenol, induced Cu(II)-dependent DNA cleavage frequently at thymine and guanine residues in DNA fragments obtained from the c-Ha-ras-1 protooncogene. When the p53 tumor suppressor gene was used, 4-nitro-2-aminophenol caused Cu(II)-dependent piperidine-labile sites at
2-Amino-5-nitrophenol.
IARC monographs on the evaluation of carcinogenic risks to humans, 57, 177-184 (1993-01-01)
Zhong-Tai Piao et al.
European journal of medicinal chemistry, 43(6), 1216-1221 (2007-10-24)
A series of 7-benzylamino-2H-1,4-benzoxazin-3(4H)-ones were synthesized using 2-amino-5-nitrophenol as a starting material. Their anticonvulsant activities were evaluated by the maximal electroshock test (MES test) and their neurotoxicity was evaluated by the rotarod neurotoxicity test (Tox.). The MES test showed that
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